Cyanoketone

Cyanoketone
Names

IUPAC name (2S,8R,9S,10R,13S,14S,17S)-17-hydroxy-4,4,10,13,17-pentamethyl-3-oxo-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-2-carbonitrile
Identifiers
CAS Registry Number	4248-66-2^Y
ChemSpider	19069^N
InChI InChI=1S/C23H33NO2/c1-20(2)18-7-6-15-16(21(18,3)12-14(13-24)19(20)25)8-10-22(4)17(15)9-11-23(22,5)26/h7,14-17,26H,6,8-12H2,1-5H3/t14-,15+,16-,17-,21+,22-,23-/m0/s1^N Key: GTBRTGPZZALPNS-MXHVRSFHSA-N^N InChI=1/C23H33NO2/c1-20(2)18-7-6-15-16(21(18,3)12-14(13-24)19(20)25)8-10-22(4)17(15)9-11-23(22,5)26/h7,14-17,26H,6,8-12H2,1-5H3/t14-,15+,16-,17-,21+,22-,23-/m0/s1 Key: GTBRTGPZZALPNS-MXHVRSFHBK
Jmol-3D images	Image
PubChem	20243
SMILES N#C[C@H]4C(=O)C(C\3=C\C[C@@H]2[C@H](CC[C@]1([C@H]2CC[C@@]1(O)C)C)[C@@]/3(C)C4)(C)C
Properties
Chemical formula	C₂₃H₃₃NO₂
Molar mass	355.51 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Cyanoketone is an androstenol. It has been shown to inhibit steroidogenesis.^[1]

It inhibits atrophy of apical dendrites.

References

↑ Di Prisco, C. L.; Materazzi, G.; Scattolini, B. (1971). "Inhibition of steroidogenesis by cyanoketone". Gynecologic investigation 2 (1): 309–315. doi:10.1159/000301873. PMID 4266510.

AR (A, B)

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).

Others

Indirect: Antigonadotropins (e.g., estrogens, progestogens, prolactin)
GnRH agonists (e,g, GnRH, leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Gonadotropins (e.g., FSH, hCG, LH)
Kisspeptin
Plasma proteins (ABP, albumin, SHBG)

See also: Estrogenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics

ER (α, β)	Agonists: 5α-Androstane-3β,17β-diol 16α-Hydroxyestrone 17α-Estradiol (alfatradiol) 17β-Estradiol (estradiol) Alestramustine Almestrone Benzestrol Bifluranol Broparestrol Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Chlorotrianisene Cloxestradiol Coumestans (e.g., coumestrol, psoralidin) DHEA Deoxymiroestrol Dienestrol Diethylstilbestrol Diethylstilbestrol diphosphate Diosgenin Doisynoestrol DPN DY-131 (GSK-9089) Epiestriol Epimestrol ERB-041 Etamestrol (eptamestrol) ERB-041 Equilenin Equilin Estetrol Estradiol benzoate Estradiol butyrylacetate Estradiol cypionate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol hemihydrate Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol palmitate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol stearate Estradiol succinate Estradiol undecylate Estradiol valerate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol succinate Estriol tripropionate Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone sulfate Estrone tetraacetylglucoside Estropipate Etamestrol Ethinylestradiol Ethinylestradiol 3-isopropylsulfonate Etynodiol diacetate FERb 033 Fenestrel Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Fosfestrol Furostilbestrol GSK-4716 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Hydroxyestrone diacetate Lignans (e.g., enterodiol, enterolactone) Mestranol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Miroestrol Moxestrol Nilestriol Orestrate Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate PPT Promestriene Promethoestrol Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranal (zearalanol)) Quinestradol Quinestrol Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenol A (BPA), DDT, parabens, PBBs, phthalates, PCBs) (R,R)-THC WAY-200070 Mixed (SERMs): 2-Hydroxyestrone (Z)-4-Hydroxytamoxifen Acolbifene Afimoxifene Arzoxifene Bazedoxifene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Epimestrol Femarelle Fispemifene GW5638 Idoxifene Lasofoxifene Levormeloxifene Menerba Mepitiostane Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Pipendoxifene Prinaberel Raloxifene SS1010 Sivifene Tamoxifen TAS-108 Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene Antagonists: Fulvestrant ICI-164384 ICI-182780 MPP PHTPP RU-58668 SS1020 (R,R)-THC XCT-790 ZK-164015 ZK-191703

GPER	Agonists: Estradiol Fulvestrant G-1 Genistein ICI-182780 Quercetin Tamoxifen Tectoridin Antagonists: G-15

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).

Others

Precursors/prohormones: Cholesterol
22R-Hydroxycholesterol
20α,22R-Dihydroxycholesterol
Pregnenolone
Pregnenolone sulfate
17-Hydroxypregnenolone
Progesterone
17-Hydroxyprogesterone
11-Deoxycortisol (cortodoxone)
DHEA
DHEA sulfate
16-Hydroxy-DHEA sulfate
5-Androstenediol
4-Androstenedione
16-Hydroxyandrostenedione
Testosterone

Indirect: Antigonadotropins (e.g., estrogens, progestogens, prolactin)
Calcitriol (vitamin D)
GnRH agonists (e,g, GnRH, leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Gonadotropins (e.g., FSH, hCG, LH)
Kisspeptin
Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics

Glucocorticoidics

Mixed (SEGRAs): Mapracorat
PF-04171327

Antagonists: Aglepristone
Asoprisnil
C108297
C113176
CORT-108297
Cyproterone acetate
Ketoconazole
Lilopristone
LLY-2707
Mifepristone
Onapristone
Org 34850
PCN
Telapristone
Toripristone
Ulipristal acetate

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 11β-HSD, 21-hydroxylase, 11β-hydroxylase, and 18-hydroxylase).

Others

See also: Androgenics • Estrogenics • Mineralocorticoidics • Progestogenics

Mineralocorticoidics

Agonists: 11-Deoxycorticosterone (desoxycortone)
11-Deoxycortisol (cortodoxone)
16α,18-Dihydroxy-11-deoxycorticosterone
17-Hydroxyaldosterone
18-Hydroxy-11-deoxycorticosterone
19-Norprogesterone
Aldosterone
Corticosterone
Desoxycortone acetate
Desoxycortone enanthate
Desoxycortone glucoside
Desoxycortone pivalate
Hydrocortisone (cortisol)
Fludrocortisone
Fludrocortisone acetate

Antagonists: 6β-Hydroxy-7α-thiomethylspironolactone
7α-Thiomethylspironolactone
17-Hydroxyprogesterone
Benidipine
Canrenoate potassium (potassium canrenoate)
Canrenoic acid
Canrenone
Dicirenone
Drospirenone
Eplerenone
Mespirenone
Mexrenoate potassium
Mexrenoic acid
Mexrenone
Oxprenoic acid
Oxprenoate potassium (RU-28318)
Pregnenolone
Progesterone
Prorenoate potassium
Prorenoic acid (prorenoate)
Prorenone
RU-26752
Spirorenone
Spironolactone
Spiroxasone

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 11β-HSD, 21-hydroxylase, 11β-hydroxylase, and 18-hydroxylase).

Others

Indirect: ACTH (corticotropin)
CRH
Plasma proteins (albumin, transcortin)
Vasopressin

See also: Androgenics • Estrogenics • Glucocorticoidics • Progestogenics

PR (A, B)

Mixed (SPRMs): Asoprisnil
Asoprisnil ecamate
Gestrinone
J1042
LG-120,838
Telapristone; Antagonistic: Mifepristone
Org-31710
Org-33628
Ulipristal acetate
ZK-137,316
ZK-230,211

Antagonists: Aglepristone
BAY-1002670
Lilopristone
Lonaprisan
Onapristone
Toripristone
ZM-150,271
ZM-172,406

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, and 21-hydroxylase).

Others

Indirect: Antigonadotropins (e.g., estrogens, progestogens, prolactin)
GnRH agonists (e,g, GnRH, leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Gonadotropins (e.g., FSH, hCG, LH)
Kisspeptin
Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics